US2014766A - Process for alkylation of aromatic bodies - Google Patents
Process for alkylation of aromatic bodies Download PDFInfo
- Publication number
- US2014766A US2014766A US723274A US72327434A US2014766A US 2014766 A US2014766 A US 2014766A US 723274 A US723274 A US 723274A US 72327434 A US72327434 A US 72327434A US 2014766 A US2014766 A US 2014766A
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- US
- United States
- Prior art keywords
- aromatic
- alkylated
- sulfonic acid
- alkylation
- bodies
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 125000003118 aryl group Chemical group 0.000 title description 17
- 238000000034 method Methods 0.000 title description 17
- 238000005804 alkylation reaction Methods 0.000 title description 9
- 230000029936 alkylation Effects 0.000 title description 8
- 150000001336 alkenes Chemical class 0.000 description 17
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 12
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 11
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 8
- 229940095050 propylene Drugs 0.000 description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 8
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- PMPBFICDXLLSRM-UHFFFAOYSA-N 1-propan-2-ylnaphthalene Chemical compound C1=CC=C2C(C(C)C)=CC=CC2=C1 PMPBFICDXLLSRM-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
- IAUKWGFWINVWKS-UHFFFAOYSA-N 1,2-di(propan-2-yl)naphthalene Chemical compound C1=CC=CC2=C(C(C)C)C(C(C)C)=CC=C21 IAUKWGFWINVWKS-UHFFFAOYSA-N 0.000 description 1
- BSMKYQUHXQAVKG-UHFFFAOYSA-N 1-nitro-2-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC=C1[N+]([O-])=O BSMKYQUHXQAVKG-UHFFFAOYSA-N 0.000 description 1
- LEVJAFQJMRYDEO-UHFFFAOYSA-N 1-propan-2-yloxy-2-propylbenzene Chemical compound CCCC1=CC=CC=C1OC(C)C LEVJAFQJMRYDEO-UHFFFAOYSA-N 0.000 description 1
- LWEAHXKXKDCSIE-UHFFFAOYSA-N 2,3-di(propan-2-yl)naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(C(C)C)C(C(C)C)=CC2=C1 LWEAHXKXKDCSIE-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- LAYPKAXEZWELEL-UHFFFAOYSA-N C(C)(C)C1=CC=CC=C1.[Cl] Chemical compound C(C)(C)C1=CC=CC=C1.[Cl] LAYPKAXEZWELEL-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical class [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930007927 cymene Natural products 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
- C07C2/70—Catalytic processes with acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/025—Sulfonic acids
Definitions
- the present invention provides a process whereby alkylation of aromatic bodies is obtained without sulfonation and in the absence of sulionating agents.
- an aromatic body can be alkylated by the direct union of an olefin therewith in the presence of a suitable sulfonic acid, without sulfonation and in the absence of sulfo'nating agents, by a simple, direct and practicable process.
- the process can be employed for the alkylation of mono-cyclic aromatic bodies such as benzene, toluene, etc., and also of polycyclic aromatic bodies such as naphthalene, anthracene, phenanthrene, etc. It can also be applied to a variety of substituted aromatic bodies such as chlor derivatives, phenols, amines, nitro derivatives, etc., and it will be understood that the expression aromatic body as used hereinafter and in the claims is intended to include such derivatives and substituted bodies,
- olefin Any suitable or desired olefin or mixture of olefins can be employed.
- olefins For example, butylene,
- propylene and amylene give rise to the correspondingly alkylated aromatic bodies such as butylated, propylated or amylated bodies, and when mixtures of olefins are employed, the alkylated bodies contain alkyl groups of various sizes.-
- the selection of the particular olefin or mixture of olefins in any case will therefore depend on considerations such as the availability of the materials and what alkyl groups it is desired to introduce into or add to the aromatic body.
- any suitable olefin bearing material may also be employed such as pressure still gas, cracked gasoline, or the like.
- the olefin and the aromatic body to be alkylated are reacted in the presence of a sultonic acid which seems to act as a carrier or catalyst in the process.
- the sulfonic acid itself may-be .alkylated in addition to the aromatic body, but
- the sulfonic acid may be either aromatic or aliphatic, lo.
- Suitable acids mentioned by way of example being benzene sulfonic acid or naphthalene sulfonic acid, ethylene di-sulfonic acid, etc.
- the quantity of sulfonic acid to be employed is not critical,
- the aromatic body or bodies to be alkylated are heated in the presence of the desired sulfonic acid and maintained at an elevated temperature, preferably betweengo to 130 C.
- the desired olefin or olefin bearing material if gaseous, is conducted into the mixture and is rapidly absorbed, or if liquid may be added to and mixed with the aromatic body and acid the quantity being sufiicient to com- 25 plete the reaction.
- the mixture should be agitated during the reaction in order to insure thorough mixing of the reagents, although this is not essential particularly when the olefin is added in liquid form.
- naphthalene where mixed with 40 gms. of naphthalene sulfonic acid and the mixture heated to a temperature between and C. Propylene gas was then conducted into the mixture, 35
- chlor benzene was treated with propylene gas in the presence of ethylene di-sultonic acid and in the manner described above. In this case the absorption of propylene was less rapid, due to the influence of the electronegative chlorine substituent, but the chlor benzene was converted to chlor cumene.
- the foregoing examples serve to illustrate the results obtained by an alkylation process embodying the invention.
- the resulting products generally comprise a series 01 more or less highly alkylated naphthalenes, which in the case of the use of propylene consisted of mono-, 'di-, triand higher isopropyl naphthalenes.
- benzene is converted to cumene and more highly alkylated benzenes, and toluene is converted into cymene, etc., when treated with propylene under a the conditions described above.
- alkylation of the substituent group may also take place together with alkylation of the nucleus.
- phenol in the example given above, was treated with propylene in the presence of di-isopropyl naphthalene sulfonic acid with the resulting production of a mixture of cumol and isopropyl cumyl ether.
- Aniline is similarly alkylated both in the benzene nucleus and in the.
- Nitro-benzol when treated in a similar manner is converted into nitro-cumene, and benzoic acid is both alkylated and esterifled.
- A- process which consists in reacting naphthalene and a suli'onic acid with an olefinic material to alkylate the naphthalene while maintaining a temperature of the order of C. to C., and recovering the alkylated naphthalene.
- a process which consists in introducing pro pylene into a mixture of naphthalene and naphthalene sulfonic acid while maintaining .a temperature of the order of 80 C. to 130 C. and recovering the propylated naphthalene.
- a process for forming alkylated aromatic hydrocarbons which consists in mixing an arcmatic hydrocarbon with an olefin while heating the reaction mixture and in the presence of a sulfonic acid, and recovering the alkylated aromatic hydrocarbon from the reaction mixture.
- a process for forming alkylated aromatic hydrocarbons which consists in reacting an olefin with an aromatic hydrocarbon in the presence of a sulfonic acid and in the absence of sulfuric acid while maintaining a temperature between the approximate limits of 80 C. and 130 C., and recovering the alkylated aromatic hydrocarbon fromthe reaction mixture.
- a process for forming alkylated aromatic hydrocarbons which consists in introducing an olefinic gas into a mixture of an aromatic hydrocarbon and a sulfonic acid in the absence of sulfuric acid while maintaining a reaction temperature of the order of 80 C. to 130 C., and recovering the afkylated aromatic hydrocarbon from the reaction mixture.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Sept. 17, 1935 UNITED STATES PATENT OFFICE PROCESS FOR ALKYLATION OF AROMATIO BODIES Robert M. Isliam, Okmulgee, th., assignor 01' three-fourths to WilliamB. Pine, Okmulgee,
Okla.
' No Drawing. Application April 30, 1934,
Serial No. 723,274
5 Claims. (Cl. 260-168 This invention relates to a process for the prowith an olefin, to the end that the aromatic l5 nucleus is alkylated and the sulfonic acid group is esterified. The aforesaid process thus results in the production of sulfonated and usually esterified products.
The present invention provides a process whereby alkylation of aromatic bodies is obtained without sulfonation and in the absence of sulionating agents. I have now discovered that an aromatic body can be alkylated by the direct union of an olefin therewith in the presence of a suitable sulfonic acid, without sulfonation and in the absence of sulfo'nating agents, by a simple, direct and practicable process.
The process can be employed for the alkylation of mono-cyclic aromatic bodies such as benzene, toluene, etc., and also of polycyclic aromatic bodies such as naphthalene, anthracene, phenanthrene, etc. It can also be applied to a variety of substituted aromatic bodies such as chlor derivatives, phenols, amines, nitro derivatives, etc., and it will be understood that the expression aromatic body as used hereinafter and in the claims is intended to include such derivatives and substituted bodies,
Any suitable or desired olefin or mixture of olefins can be employed. For example, butylene,
propylene and amylene give rise to the correspondingly alkylated aromatic bodies such as butylated, propylated or amylated bodies, and when mixtures of olefins are employed, the alkylated bodies contain alkyl groups of various sizes.- The selection of the particular olefin or mixture of olefins in any case will therefore depend on considerations such as the availability of the materials and what alkyl groups it is desired to introduce into or add to the aromatic body. Instead of pure olefins or, mixtures thereof, any suitable olefin bearing material may also be employed such as pressure still gas, cracked gasoline, or the like. The olefin and the aromatic body to be alkylated are reacted in the presence of a sultonic acid which seems to act as a carrier or catalyst in the process. The sulfonic acid itself may-be .alkylated in addition to the aromatic body, but
this does not interfere with the desiredalkyla- 5 tion of the aromatic bodies themselves, the latter after alkylation being separated and recovered from the sulfonic acid and the sulfonic acid being preferably recovered for further use. The sulfonic acid may be either aromatic or aliphatic, lo.
suitable acids mentioned by way of example being benzene sulfonic acid or naphthalene sulfonic acid, ethylene di-sulfonic acid, etc. The quantity of sulfonic acid to be employed is not critical,
since the'acid acts as a carrier and is contin- 15.
uously regenerated during the reaction.
In carrying out the process, the aromatic body or bodies to be alkylated are heated in the presence of the desired sulfonic acid and maintained at an elevated temperature, preferably betweengo to 130 C. The desired olefin or olefin bearing material, if gaseous, is conducted into the mixture and is rapidly absorbed, or if liquid may be added to and mixed with the aromatic body and acid the quantity being sufiicient to com- 25 plete the reaction. In general, the mixture should be agitated during the reaction in order to insure thorough mixing of the reagents, although this is not essential particularly when the olefin is added in liquid form. 30
In a typical example of the process, 40 gms. of
naphthalene where mixed with 40 gms. of naphthalene sulfonic acid and the mixture heated to a temperature between and C. Propylene gas was then conducted into the mixture, 35
when the mixture was allowed to cool. This solidified layer was then removed and again melted 45 over hot water and allowed to crystallize by cooling, the alkylated naphthalene then being separated and distilled. The bulk of this product distilled at a temperature of 329 to 331 C. and consisted of di-isopropyl naphthalene. amounts of mono-isopropyl naphthalene and of triand tetra-isopropyl naphthalene were also present.
The water washings were then evaporated and the sulfonic acid recovered for further use. 66
Small 50 v propyl phenyl isopropyl ether) by extraction with sodium hydroxide solution. Approximately 20% of the mixture was cumol and the remaining 80 was principally isopropyl cumyl ether.
In a further example chlor benzene was treated with propylene gas in the presence of ethylene di-sultonic acid and in the manner described above. In this case the absorption of propylene was less rapid, due to the influence of the electronegative chlorine substituent, but the chlor benzene was converted to chlor cumene.
The foregoing examples serve to illustrate the results obtained by an alkylation process embodying the invention. When naphthalene and the like are alkylated, the resulting products generally comprise a series 01 more or less highly alkylated naphthalenes, which in the case of the use of propylene consisted of mono-, 'di-, triand higher isopropyl naphthalenes. Similarly, benzene is converted to cumene and more highly alkylated benzenes, and toluene is converted into cymene, etc., when treated with propylene under a the conditions described above. When the invention is employed for the alkylation of substituted aromatic bodies, and the substituent group is reactive as in the case of phenols and amines for example, alkylation of the substituent group may also take place together with alkylation of the nucleus. Thus phenol, in the example given above, was treated with propylene in the presence of di-isopropyl naphthalene sulfonic acid with the resulting production of a mixture of cumol and isopropyl cumyl ether. Aniline is similarly alkylated both in the benzene nucleus and in the.
amino group. Nitro-benzol when treated in a similar manner is converted into nitro-cumene, and benzoic acid is both alkylated and esterifled.
It will be understood that the invention is not limited to the specific examples given above and that other aromatic bodies, olefins or olefin-bearing materials, and sulionic acids, either aromatic or aliphatic, may be employed as starting materials. The specific materials employed in carrying out the process will accordingly vary depending on materials available and the uses to which the product is to be put, and the proportions and the details 01' the procedure may also be varied without departing from the spirit of the invention. Reference will therefore be had to the, appendedclaims tor a definition of the limits oi.
the invention. What'is claimed is:
-, 1. A- process which consists in reacting naphthalene and a suli'onic acid with an olefinic material to alkylate the naphthalene while maintaining a temperature of the order of C. to C., and recovering the alkylated naphthalene.
2. A process which consists in introducing pro pylene into a mixture of naphthalene and naphthalene sulfonic acid while maintaining .a temperature of the order of 80 C. to 130 C. and recovering the propylated naphthalene.
3. A process for forming alkylated aromatic hydrocarbons which consists in mixing an arcmatic hydrocarbon with an olefin while heating the reaction mixture and in the presence of a sulfonic acid, and recovering the alkylated aromatic hydrocarbon from the reaction mixture.
4. A process for forming alkylated aromatic hydrocarbons which consists in reacting an olefin with an aromatic hydrocarbon in the presence of a sulfonic acid and in the absence of sulfuric acid while maintaining a temperature between the approximate limits of 80 C. and 130 C., and recovering the alkylated aromatic hydrocarbon fromthe reaction mixture.
5. A process for forming alkylated aromatic hydrocarbons. which consists in introducing an olefinic gas into a mixture of an aromatic hydrocarbon and a sulfonic acid in the absence of sulfuric acid while maintaining a reaction temperature of the order of 80 C. to 130 C., and recovering the afkylated aromatic hydrocarbon from the reaction mixture.
ROBERT M. ISHAM.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US723274A US2014766A (en) | 1934-04-30 | 1934-04-30 | Process for alkylation of aromatic bodies |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US723274A US2014766A (en) | 1934-04-30 | 1934-04-30 | Process for alkylation of aromatic bodies |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2014766A true US2014766A (en) | 1935-09-17 |
Family
ID=24905570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US723274A Expired - Lifetime US2014766A (en) | 1934-04-30 | 1934-04-30 | Process for alkylation of aromatic bodies |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2014766A (en) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2462793A (en) * | 1945-08-09 | 1949-02-22 | Pan American Refining Corp | Alkylation and catalyst recovery |
| US2462792A (en) * | 1945-08-09 | 1949-02-22 | Pan American Refining Corp | Alkylation process |
| US2564077A (en) * | 1948-12-11 | 1951-08-14 | Standard Oil Co | Alkenylation process |
| US2567854A (en) * | 1947-05-30 | 1951-09-11 | Shell Dev | Production of alkyl aromatic sulfonic acids and their salts |
| US2575807A (en) * | 1943-04-13 | 1951-11-20 | Atlantic Refining Co | Fat splitting agent and method of producing same |
| US2585983A (en) * | 1948-12-04 | 1952-02-19 | Standard Oil Co | Alkylation process |
| US2714120A (en) * | 1950-05-23 | 1955-07-26 | Goodrich Co B F | Method of preparing aralkylated phenolic compounds |
| US3116336A (en) * | 1963-12-31 | Alkylation process | ||
| US3177259A (en) * | 1963-08-20 | 1965-04-06 | Shell Oil Co | Alkylation process |
| US3376212A (en) * | 1966-02-10 | 1968-04-02 | United States Steel Corp | Method of preventing crystals from forming in creosote and the resulting product |
| US3932537A (en) * | 1971-09-09 | 1976-01-13 | Reichhold Chemicals, Inc. | Alkylation of phenols |
| US3959399A (en) * | 1975-02-19 | 1976-05-25 | Nalco Chemical Company | Mono-alkylation of naphthalene |
| US3962365A (en) * | 1975-05-28 | 1976-06-08 | Koppers Company, Inc. | Process for producing a mixture of isopropylnaphthalenes |
| US4255343A (en) * | 1979-08-13 | 1981-03-10 | E. I. Du Pont De Nemours And Company | Preparation of 2-T-alkylanthracene |
| US5072047A (en) * | 1989-10-10 | 1991-12-10 | The Dow Chemical Company | Ortho-alkylation of aromatic amines |
-
1934
- 1934-04-30 US US723274A patent/US2014766A/en not_active Expired - Lifetime
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3116336A (en) * | 1963-12-31 | Alkylation process | ||
| US2575807A (en) * | 1943-04-13 | 1951-11-20 | Atlantic Refining Co | Fat splitting agent and method of producing same |
| US2462792A (en) * | 1945-08-09 | 1949-02-22 | Pan American Refining Corp | Alkylation process |
| US2462793A (en) * | 1945-08-09 | 1949-02-22 | Pan American Refining Corp | Alkylation and catalyst recovery |
| US2567854A (en) * | 1947-05-30 | 1951-09-11 | Shell Dev | Production of alkyl aromatic sulfonic acids and their salts |
| US2585983A (en) * | 1948-12-04 | 1952-02-19 | Standard Oil Co | Alkylation process |
| US2564077A (en) * | 1948-12-11 | 1951-08-14 | Standard Oil Co | Alkenylation process |
| US2714120A (en) * | 1950-05-23 | 1955-07-26 | Goodrich Co B F | Method of preparing aralkylated phenolic compounds |
| US3177259A (en) * | 1963-08-20 | 1965-04-06 | Shell Oil Co | Alkylation process |
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| US5072047A (en) * | 1989-10-10 | 1991-12-10 | The Dow Chemical Company | Ortho-alkylation of aromatic amines |
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